Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares

Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares

The n-octanol/water partition coefficient (log KOW) is a useful parameter for the assessment of the environmental fate and impact of xenobiotic trace contaminants. Quantitative structure-activity relationship (QSAR) model for log KOW of polychlorinated biphenyls (PCBs) was analyzed by using the dens...

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Main Authors: Fang-Li Zhang, Xing-Jian Yang, Xiu-Ling Xue, Xue-Qin Tao, Gui-Ning Lu, Zhi Dang
Format: Article
Language:English
Published: Hindawi Limited 2013-01-01
Series:Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2013/740548
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spelling doaj-9f1df32f9ce8410587c559b711c5bd1a2020-11-24T23:08:18ZengHindawi LimitedJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/740548740548Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least SquaresFang-Li Zhang0Xing-Jian Yang1Xiu-Ling Xue2Xue-Qin Tao3Gui-Ning Lu4Zhi Dang5School of Environment and Energy, South China University of Technology, Guangzhou 510006, ChinaSchool of Environment and Energy, South China University of Technology, Guangzhou 510006, ChinaCollege of Chemical Engineering, Huaqiao University, Xiamen 361021, ChinaSchool of Environmental Science and Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, ChinaSchool of Environment and Energy, South China University of Technology, Guangzhou 510006, ChinaSchool of Environment and Energy, South China University of Technology, Guangzhou 510006, ChinaThe n-octanol/water partition coefficient (log KOW) is a useful parameter for the assessment of the environmental fate and impact of xenobiotic trace contaminants. Quantitative structure-activity relationship (QSAR) model for log KOW of polychlorinated biphenyls (PCBs) was analyzed by using the density functional theory at B3LYP/6-31G(d) level and the partial least squares (PLS) method with an optimizing procedure. A PLS model with reasonably good coefficient (R2=0.992) and cross-validation test (Q2cum=0.988) values was obtained. All the predicted values are within the range of ±0.3 log unit from the observed values. The log KOW values of 7 PCBs in the test set predicted by the model are very close to those observed, indicating that this model has high fitting precision and good predictability. The PLS analysis showed that PCBs with larger electronic spatial extent and lower molecular total energy values tend to be more hydrophobic and lipophilic.http://dx.doi.org/10.1155/2013/740548
collection DOAJ
language English
format Article
sources DOAJ
author Fang-Li Zhang
Xing-Jian Yang
Xiu-Ling Xue
Xue-Qin Tao
Gui-Ning Lu
Zhi Dang
spellingShingle Fang-Li Zhang
Xing-Jian Yang
Xiu-Ling Xue
Xue-Qin Tao
Gui-Ning Lu
Zhi Dang
Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
Journal of Chemistry
author_facet Fang-Li Zhang
Xing-Jian Yang
Xiu-Ling Xue
Xue-Qin Tao
Gui-Ning Lu
Zhi Dang
author_sort Fang-Li Zhang
title Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
title_short Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
title_full Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
title_fullStr Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
title_full_unstemmed Estimation of n-Octanol/Water Partition Coefficients (log KOW) of Polychlorinated Biphenyls by Using Quantum Chemical Descriptors and Partial Least Squares
title_sort estimation of n-octanol/water partition coefficients (log kow) of polychlorinated biphenyls by using quantum chemical descriptors and partial least squares
publisher Hindawi Limited
series Journal of Chemistry
issn 2090-9063
2090-9071
publishDate 2013-01-01
description The n-octanol/water partition coefficient (log KOW) is a useful parameter for the assessment of the environmental fate and impact of xenobiotic trace contaminants. Quantitative structure-activity relationship (QSAR) model for log KOW of polychlorinated biphenyls (PCBs) was analyzed by using the density functional theory at B3LYP/6-31G(d) level and the partial least squares (PLS) method with an optimizing procedure. A PLS model with reasonably good coefficient (R2=0.992) and cross-validation test (Q2cum=0.988) values was obtained. All the predicted values are within the range of ±0.3 log unit from the observed values. The log KOW values of 7 PCBs in the test set predicted by the model are very close to those observed, indicating that this model has high fitting precision and good predictability. The PLS analysis showed that PCBs with larger electronic spatial extent and lower molecular total energy values tend to be more hydrophobic and lipophilic.
url http://dx.doi.org/10.1155/2013/740548
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